Did you go from eating everything to only eating meals prepared by yourself?

I do let others cook for me. But I've 'trained' my BF to weigh his ingredients when he cooks, which was a requirement for me: since we alternate cooking dinner, I can't afford to guesstimate one dinner in two.

Aside from that, I go to a restaurant once every few weeks and I eat at friends/family once every few weeks.
I guesstimate portions and ingredients, erring on the side of overestimating. I either use nutritional data from restaurant chains or 'decompose' the dish mentally and log the ingredients.
You could also use a portable food scale, if you feel comfortable doing that. That way, even if you're not sure about the ingredients, at least there isn't the uncertainty of the portion size.

I've lost weight without issues, and that was even on a small deficit of around 250kcal a day, which requires more precision that a large deficit.

If I'm going out for a meal then I usually guesstimate and accept that it probably isn't accurate.
I try to make sensible choices and if not then I do the best I can to log it and move on.
I think that if you're having 95% of your meals at home or prepared by you then you can afford a meal out.
It's all about what you do most of the time rather than what you do on occasion.

I live in a household with multiple adults and cooking time was always stressful due to some people being picky eaters. I recently decided that since we're all adults, everyone can be responsible for their own food which has made my progress great. I weigh my own food except for the rare times I eat out and then I guesstimate what I have to.

I cook all of my own meals unless I go out to eat, which at most is only 1-2 days/wk on weekend for brunch.

I do not eat any "fast food;" only at cafes/restaurants for dine-in meals where Covid precautions are observed.

I do all the cooking at home, with the exception of Sunday night dinner - hubs and I eat with his folks and they cook. But I know how they cook, so I'm confident in my guesstimates. We do occasionally get restaurant food, but I've been both cooking and logging long enough to also be confident in my guesstimates there, and a lot of the places we go to do actually publish nutrition information. Or if they don't, their fare is close enough to a national chain that does for jazz (e.g., there's a local bbq place that doesn't have calorie info on their menu, but they serve pretty standard bbq restaurant fare, so I sub entries from Sonny's or some other bbq chain).

If WW is working for you, by all means do what works, but I've found just straight calorie-counting to be the most effective for me. My two issues with WW are that (1) you don't actually learn much of anything about nutrition, as the formula for calculating points obfuscates a lot of that information, and (2) all food has calories, even the stuff on the "zero-points" list. At the end of the day, it comes down to calories in vs calories out, so it's really easy to overeat the "zero points" foods and thus either not lose or indeed gain weight. The body doesn't know or care if you take in 3000 calories' worth of Ding Dongs or Brussels sprouts, if that's more than it needs right now, the excess gets stored as fat. Food isn't magic, it's just fuel. There's no real trick to it, it's just math.